Dantron (BioDeep_00000002382)

Main id: BioDeep_00000406552

 

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


InChI=1/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16

化学式: C14H8O4 (240.0422568)
中文名称: 1,8-二羟基蒽醌, 丹蒽醌
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
InChI: InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H

描述信息

Danthron is an orange crystalline powder. Almost odorless and tasteless. (NTP, 1992)
Chrysazin is a dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8. It has a role as an apoptosis inducer and a plant metabolite.
Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.
Danthron is a natural product found in Didemnum albopunctatum, Asphodelus tenuifolius, and other organisms with data available.
Danthron is a reddish, synthetic anthraquinone derivative. Danthron has been widely used as a laxative, but is no longer used to treat constipation and is currently used as an antioxidant in synthetic lubricants, in the synthesis of experimental antitumor agents, as a fungicide and as an intermediate for making dyes. This substance is a suspected mutagen and is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. (NCI05)
A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AB - Contact laxatives
A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.
Dantron is found in green vegetables. Dantron occurs in roots of Rheum palmatum (Turkey rhubarb
Occurs in roots of Rheum palmatum (Turkey rhubarb). Dantron is found in green vegetables.
D005765 - Gastrointestinal Agents > D002400 - Cathartics
D009676 - Noxae > D009153 - Mutagens
[Raw Data] CB120_Laxapur_neg_20eV_000028.txt
[Raw Data] CB120_Laxapur_neg_40eV_000028.txt
[Raw Data] CB120_Laxapur_neg_30eV_000028.txt
[Raw Data] CB120_Laxapur_neg_10eV_000028.txt
[Raw Data] CB120_Laxapur_neg_50eV_000028.txt
Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.
Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.
Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.

同义名列表

111 个代谢物同义名

InChI=1/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16; Dantron; Chrysazin;1,8-Dihydroxyanthraquinone;1,4,5,8-tetroxyantraquinone; 1,8-Dihydroxyanthraquinone, Vetec(TM) reagent grade, 96\\%; 1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione; 1,8-Dihydroxyanthracene-9,10-dione (Danthron); Danthron (1,8-Dihydroxyanthracene-9,10-dione); 1,8-Dihydroxy-9,10-anthracenedione, 9CI; 1,8-bis(oxidanyl)anthracene-9,10-dione; 9,10-Anthracenedione, 1,8-dihydroxy-; 1,8-Dihydroxyanthra-9,10-quinone #; 1,8-Dihydroxy-9,10-anthracenedione; DITHRANOL IMPURITY B [EP IMPURITY]; 1,8-Dihydroxyanthracene-9,10-dione; 1,8-Dihydroxyanthrachinon [Czech]; 1,8-Dihydroxyanthra-9,10-quinone; 1,8-Dihydroxyanthraquinone, 96\\%; 8,9-dihydroxy-1,10-anthraquinone; 1,8-dihydroxy-9,10-anthraquinone; 1,8-Dihydroxyanthraquinone ,(S); Anthraquinone, 1,8-dihydroxy-; 1,8-dihydroxy-anthraquinone; 1,4,5,8-Tetroxyantraquinone; 1,8-dihydroxyanthraquinone; Anthraquinone,8-dihydroxy-; 1,8-Dihydroxyanthrachinon; Pilules Vinchy N.F. (TN); 1,8-Dihydroanthraquinone; dihyanthraquin_P21/n_LT; component of Dorbantyl; Dantrona [INN-Spanish]; 1,8-Dioxyanthraquinone; dihyanthraquin_P41_LT; Dantronum [INN-Latin]; Dantrone [INN-French]; Dorbantyl (Salt/Mix); component of Doxidan; Dioxyanthrachinonum; Dorbanex (Salt/Mix); Pilules Vinchy N.F.; component of Modane; component of Doxan; 9, 1,8-dihydroxy-; Spectrum3_000650; Spectrum5_000324; DANTRON [WHO-DD]; DANTHRON [VANDF]; Spectrum2_000603; Spectrum4_001682; UNII-Z4XE6IBF3V; DANTHRON [HSDB]; DANTRON [MART.]; DANTRON [IARC]; Danthron [USP]; Tox21_111122_1; Dantron (INN); DANTHRON [MI]; Dantron [INN]; Danthron, BAN; MEGxp0_001693; DivK1c_000284; Dantron, INN; Tox21_200986; NCI60_041443; KBio2_007366; KBio2_004798; KBio1_000284; Tox21_111122; KBio3_001479; ACon1_000135; KBio2_002230; IDI1_000284; Laxanthreen; Usaf nd-59; Antrapurol; Z4XE6IBF3V; Chrysazine; Neokutin S; Criasazin; Laxipurin; danthrone; Zwitsalax; AI3-38117; chrysazin; Scatron D; Dantronum; Istizine; Dantrone; Danthane; Danthron; Diaquone; Dorbanex; Dantrona; Pastomin; Laxanorm; Laxapur; Istizin; Dantron; Laxipur; Dionone; Dorbane; Danivac; Duolax; Roydan; Bancon; Prugol; Altan; Istan; 3nsq; LTAN; CHZ; Danthron



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Razieh Amini, Shadi Moradi, Rezvan Najafi, Mehrdokht Mazdeh, Amir Taherkhani. BACE1 Inhibition Utilizing Organic Compounds Holds Promise as a Potential Treatment for Alzheimer's and Parkinson's Diseases. Oxidative medicine and cellular longevity. 2024; 2024(?):6654606. doi: 10.1155/2024/6654606. [PMID: 38425997]
  • Stephan Chalon, M Farouk Chughlay, Nada Abla, Andre Marie Tchouatieu, Amina Haouala, Ben Hutter, Ulrike Lorch, Fiona Macintyre. Unanticipated CNS Safety Signal in a Placebo-Controlled, Randomized Trial of Co-Administered Atovaquone-Proguanil and Amodiaquine. Clinical pharmacology and therapeutics. 2022 04; 111(4):867-877. doi: 10.1002/cpt.2404. [PMID: 34453327]
  • Bruno A Rodriguez-Rodriguez, Maria G Noval, Maria E Kaczmarek, Kyung Ku Jang, Sara A Thannickal, Angelica Cifuentes Kottkamp, Rebecca S Brown, Margaret Kielian, Ken Cadwell, Kenneth A Stapleford. Atovaquone and Berberine Chloride Reduce SARS-CoV-2 Replication In Vitro. Viruses. 2021 12; 13(12):. doi: 10.3390/v13122437. [PMID: 34960706]
  • Namshik Han, Woochang Hwang, Konstantinos Tzelepis, Patrick Schmerer, Eliza Yankova, Méabh MacMahon, Winnie Lei, Nicholas M Katritsis, Anika Liu, Ulrike Felgenhauer, Alison Schuldt, Rebecca Harris, Kathryn Chapman, Frank McCaughan, Friedemann Weber, Tony Kouzarides. Identification of SARS-CoV-2-induced pathways reveals drug repurposing strategies. Science advances. 2021 06; 7(27):. doi: 10.1126/sciadv.abh3032. [PMID: 34193418]
  • Chuanrui Ma, Zhongyan Wang, Ronglin Xia, Lingling Wei, Chao Zhang, Jing Zhang, Linna Zhao, Han Wu, Lin Kang, Shu Yang. Danthron ameliorates obesity and MAFLD through activating the interplay between PPARα/RXRα heterodimer and adiponectin receptor 2. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111344. doi: 10.1016/j.biopha.2021.111344. [PMID: 33581653]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Xiujin Shi, Yi Zhang, Baidi Lin, Yang Zhou, Wei Suo, Juanjuan Wei, Lin Zhang, Jie Lin, Fucheng Xiao, Limin Zhao, Yang Lin. Danthron attenuates experimental atherosclerosis by targeting foam cell formation. Experimental physiology. 2021 03; 106(3):653-662. doi: 10.1113/ep089021. [PMID: 33450102]
  • John Oludele Olanlokun, Folashade Abimbola Balogun, Olufunso Olabode Olorunsogo. Chemotherapeutic and prophylactic antimalarial drugs induce cell death through mitochondrial-mediated apoptosis in murine models. Drug and chemical toxicology. 2021 Jan; 44(1):47-57. doi: 10.1080/01480545.2018.1536139. [PMID: 30486696]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Ryohkan Funakoshi, Yukana Tomoda, Toshiyuki Kudo, Kenichi Furihata, Hiroyuki Kusuhara, Kiyomi Ito. Effects of proton pump inhibitors, esomeprazole and vonoprazan, on the disposition of proguanil, a CYP2C19 substrate, in healthy volunteers. British journal of clinical pharmacology. 2019 07; 85(7):1454-1463. doi: 10.1111/bcp.13914. [PMID: 30845361]
  • Pablo Villoslada, Gemma Vila, Valeria Colafrancesco, Beatriz Moreno, Begoña Fernandez-Diez, Raquel Vazquez, Inna Pertsovskaya, Irati Zubizarreta, Irene Pulido-Valdeolivas, Joaquin Messeguer, Gloria Vendrell-Navarro, Jose Maria Frade, Noelia López-Sánchez, Meritxell Teixido, Ernest Giralt, Mar Masso, Jason C Dugas, Dmitri Leonoudakis, Karen D Lariosa-Willingham, Lawrence Steinman, Angel Messeguer. Axonal and Myelin Neuroprotection by the Peptoid BN201 in Brain Inflammation. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2019 07; 16(3):808-827. doi: 10.1007/s13311-019-00717-4. [PMID: 30815844]
  • Sameer Shakeel Ansari, Rizwan Hasan Khan, Saeeda Naqvi. Probing the intermolecular interactions into serum albumin and anthraquinone systems: a spectroscopic and docking approach. Journal of biomolecular structure & dynamics. 2018 Oct; 36(13):3362-3375. doi: 10.1080/07391102.2017.1388284. [PMID: 28974158]
  • C Anisha, P Sachidanandan, E K Radhakrishnan. Endophytic Paraconiothyrium sp. from Zingiber officinale Rosc. Displays Broad-Spectrum Antimicrobial Activity by Production of Danthron. Current microbiology. 2018 Mar; 75(3):343-352. doi: 10.1007/s00284-017-1387-7. [PMID: 29101453]
  • Maarten van der Velden, Albert Bilos, Jeroen J M W van den Heuvel, Sanna R Rijpma, Evelien G E Hurkmans, Robert W Sauerwein, Frans G M Russel, Jan B Koenderink. Proguanil and cycloguanil are organic cation transporter and multidrug and toxin extrusion substrates. Malaria journal. 2017 10; 16(1):422. doi: 10.1186/s12936-017-2062-y. [PMID: 29061131]
  • Maxime G Corral, Julie Leroux, Keith A Stubbs, Joshua S Mylne. Herbicidal properties of antimalarial drugs. Scientific reports. 2017 03; 7(?):45871. doi: 10.1038/srep45871. [PMID: 28361906]
  • Fabrice Bruneel, Florence Tubach, Jean-Paul Mira, Sandrine Houze, Sebastien Gibot, Marie-Genevieve Huisse, Bruno Megarbane, Christophe Choquet, Philippe Corne, Eric Peytel, Daniel Villers, Christophe Camus, Olivier Bouchaud, Eric Caumes, Pierre-Marie Girard, Fabrice Simon, Antoine Kalloumeh, Carine Roy, Remy Durand, Jacques Le Bras, Sophie Matheron, Michel Wolff. Imported falciparum malaria in adults: host- and parasite-related factors associated with severity. The French prospective multicenter PALUREA cohort study. Intensive care medicine. 2016 Oct; 42(10):1588-1596. doi: 10.1007/s00134-016-4356-x. [PMID: 27169586]
  • Domagoj Dinter, Goran Gajski, Ana-Marija Domijan, Vera Garaj-Vrhovac. Cytogenetic and oxidative status of human lymphocytes after exposure to clinically relevant concentrations of antimalarial drugs atovaquone and proguanil hydrochloride in vitro. Fundamental & clinical pharmacology. 2015 Dec; 29(6):575-85. doi: 10.1111/fcp.12153. [PMID: 26434663]
  • Mario Thevis, Hans Geyer, Andreas Thomas, Laura Tretzel, Isabelle Bailloux, Corinne Buisson, Francoise Lasne, Maximilian S Schaefer, Peter Kienbaum, Irmela Mueller-Stoever, Wilhelm Schänzer. Formation of the diuretic chlorazanil from the antimalarial drug proguanil--implications for sports drug testing. Journal of pharmaceutical and biomedical analysis. 2015 Nov; 115(?):208-13. doi: 10.1016/j.jpba.2015.07.017. [PMID: 26226108]
  • Aditya Arvindekar, Tanaji More, Pavan V Payghan, Kirti Laddha, Nanda Ghoshal, Akalpita Arvindekar. Evaluation of anti-diabetic and alpha glucosidase inhibitory action of anthraquinones from Rheum emodi. Food & function. 2015 Aug; 6(8):2693-700. doi: 10.1039/c5fo00519a. [PMID: 26145710]
  • Andrea K Boggild, Rachel Lau, Denis Reynaud, Kevin C Kain, Marvin Gerson. Failure of atovaquone-proguanil malaria chemoprophylaxis in a traveler to Ghana. Travel medicine and infectious disease. 2015 Jan; 13(1):89-93. doi: 10.1016/j.tmaid.2014.12.010. [PMID: 25582377]
  • Martin Lochner, Andrew J Thompson. The antimalarial drug proguanil is an antagonist at 5-HT3 receptors. The Journal of pharmacology and experimental therapeutics. 2014 Dec; 351(3):674-84. doi: 10.1124/jpet.114.218461. [PMID: 25277140]
  • Aiko Iguchi, Nobuyuki Shiranaga, Aya Matsuu, Yoshiaki Hikasa. Efficacy of Malarone(®) in dogs naturally infected with Babesia gibsoni. The Journal of veterinary medical science. 2014 Sep; 76(9):1291-5. doi: 10.1292/jvms.14-0139. [PMID: 24909969]
  • Qigui Li, Shon Remich, Scott R Miller, Bernhards Ogutu, Walter Otieno, Victor Melendez, Paktiya Teja-Isavadharm, Peter J Weina, Mark R Hickman, Bryan Smith, Mark Polhemus. Pharmacokinetic evaluation of intravenous artesunate in adults with uncomplicated falciparum malaria in Kenya: a phase II study. Malaria journal. 2014 Jul; 13(?):281. doi: 10.1186/1475-2875-13-281. [PMID: 25047305]
  • Carmelina Calitri, Silvia Garazzino, Roberta Camilla, Licia Peruzzi, Alessandro Amore, Pier-Angelo Tovo. 'Collateral' effect of artemether in an atypical kidney involvement by Plasmodium falciparum malaria: a case report. Journal of vector borne diseases. 2014 Jun; 51(2):147-8. doi: NULL. [PMID: 24947225]
  • Rong Zhou, Ling Wang, Xing Xu, Jing Chen, Li-hong Hu, Li-li Chen, Xu Shen. Danthron activates AMP-activated protein kinase and regulates lipid and glucose metabolism in vitro. Acta pharmacologica Sinica. 2013 Aug; 34(8):1061-9. doi: 10.1038/aps.2013.39. [PMID: 23770982]
  • Eleri Wallace, Charlene M Y Ong, Charles M Heard. Delivery of atovaquone and proguanil across sublingual membranes, in vitro. Pharmaceutical development and technology. 2012 Nov; 17(6):770-6. doi: 10.3109/10837450.2011.580760. [PMID: 21612571]
  • M Cella, F Kloprogge, M Danhof, O Della Pasqua. Dosing rationale for fixed-dose combinations in children: shooting from the hip?. Clinical pharmacology and therapeutics. 2012 Apr; 91(4):718-25. doi: 10.1038/clpt.2011.297. [PMID: 22398964]
  • . Toxicology study of senna (CAS No. 8013-11-4) in C57BL/6NTAC Mice and toxicology and carcinogenesis study of senna in genetically modified C3B6.129F1/Tac-Trp53tm1Brd haploinsufficient mice (Feed Studies). National Toxicology Program genetically modified model report. 2012 Apr; ?(15):1-114. doi: . [PMID: 23001288]
  • Jie Tian, Xuan Chen, Xiaohong Bai. Comparison of dispersive liquid-liquid microextraction based on organic solvent and ionic liquid combined with high-performance liquid chromatography for the analysis of emodin and its metabolites in urine samples. Journal of separation science. 2012 Jan; 35(1):145-52. doi: 10.1002/jssc.201100729. [PMID: 22144110]
  • Pius S Fasinu, Patrick J Bouic, Bernd Rosenkranz. An overview of the evidence and mechanisms of herb-drug interactions. Frontiers in pharmacology. 2012; 3(?):69. doi: 10.3389/fphar.2012.00069. [PMID: 22557968]
  • Samuel Takashi Saito, Danielle da Silva Trentin, Alexandre José Macedo, Cristina Pungartnik, Grace Gosmann, Jaqueline de Deos Silveira, Temenouga Nikolova Guecheva, João Antonio Pêgas Henriques, Martin Brendel. Bioguided Fractionation Shows Cassia alata Extract to Inhibit Staphylococcus epidermidis and Pseudomonas aeruginosa Growth and Biofilm Formation. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):867103. doi: 10.1155/2012/867103. [PMID: 22548121]
  • Wenshuo Zhang, Robert M Sargis, Paul A Volden, Christopher M Carmean, Xiao J Sun, Matthew J Brady. PCB 126 and other dioxin-like PCBs specifically suppress hepatic PEPCK expression via the aryl hydrocarbon receptor. PloS one. 2012; 7(5):e37103. doi: 10.1371/journal.pone.0037103. [PMID: 22615911]
  • Akinsomisoye Olumide Stephen, Raji Yinusa. Prolonged administration of proguanil induces reproductive toxicity in male rats. The Journal of toxicological sciences. 2011 Oct; 36(5):587-99. doi: 10.2131/jts.36.587. [PMID: 22008534]
  • Hong Yang, Li-na Xu, Cheng-yan He, Xin Liu, Rou-yu Fang, Tong-hui Ma. CFTR chloride channel as a molecular target of anthraquinone compounds in herbal laxatives. Acta pharmacologica Sinica. 2011 Jun; 32(6):834-9. doi: 10.1038/aps.2011.46. [PMID: 21602836]
  • Chiara Tommasi, Rita Bellagamba, Massimo Tempestilli, Antonio D'Avolio, Anna L Gallo, Jelena Ivanovic, Emanuele Nicastri, Leopoldo P Pucillo, Pasquale Narciso. Marked increase in etravirine and saquinavir plasma concentrations during atovaquone/proguanil prophylaxis. Malaria journal. 2011 May; 10(?):141. doi: 10.1186/1475-2875-10-141. [PMID: 21600016]
  • Maher Kammoun, Sonia Miladi, Yassine Ben Ali, Mohamed Damak, Youssef Gargouri, Sofiane Bezzine. In vitro study of the PLA2 inhibition and antioxidant activities of Aloe vera leaf skin extracts. Lipids in health and disease. 2011 Feb; 10(?):30. doi: 10.1186/1476-511x-10-30. [PMID: 21310091]
  • Weijun Kong, Xinhua Xia, Jiabo Wang, Canping Zhou, Fang Fang, Xiaoyan Xing, Cheng Jin, Yanling Zhao, Qingce Zang, Xiaohe Xiao. Solid-phase extraction and ultra high-performance liquid chromatography tandem mass spectrometry analysis of the gastrointestinal absorption of emodin in different digestive segments of rats. Journal of separation science. 2011 Feb; 34(3):260-7. doi: 10.1002/jssc.201000757. [PMID: 21268248]
  • Haitao Zhang, Rong Zhou, Li Li, Jing Chen, Lili Chen, Chenjing Li, Hong Ding, Liang Yu, Lihong Hu, Hualiang Jiang, Xu Shen. Danthron functions as a retinoic X receptor antagonist by stabilizing tetramers of the receptor. The Journal of biological chemistry. 2011 Jan; 286(3):1868-75. doi: 10.1074/jbc.m110.166215. [PMID: 21084305]
  • Robert L Clark, William E Gristwood, Richard Lewsley, Robert Wilson, Andrew W Harrell. Localization of artesunate and its derivatives in the pregnant rat and fetus following oral administration and relationship to developmental toxicity. Birth defects research. Part B, Developmental and reproductive toxicology. 2010 Oct; 89(5):364-75. doi: 10.1002/bdrb.20256. [PMID: 20717981]
  • Hetty Jolink, Jan den Hartigh, Leo G Visser, Cees van Nieuwkoop. Pancytopenia due to proguanil toxicity in a returning traveller with fever. European journal of clinical pharmacology. 2010 Aug; 66(8):811-2. doi: 10.1007/s00228-010-0824-3. [PMID: 20407763]
  • Matthijs van Luin, Marchina E Van der Ende, Clemens Richter, Mirjam Visser, Diari Faraj, Andre Van der Ven, Luc Gelinck, Frank Kroon, Ferdinand W Wit, Ron H N Van Schaik, Paul F M Kuks, David M Burger. Lower atovaquone/proguanil concentrations in patients taking efavirenz, lopinavir/ritonavir or atazanavir/ritonavir. AIDS (London, England). 2010 May; 24(8):1223-6. doi: 10.1097/qad.0b013e3283389129. [PMID: 20299957]
  • Julius Olugbenga Soyinka, Cyprian Ogbonna Onyeji. Alteration of pharmacokinetics of proguanil in healthy volunteers following concurrent administration of efavirenz. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2010 Feb; 39(4):213-8. doi: 10.1016/j.ejps.2009.11.012. [PMID: 19961932]
  • David J Bell, Dan Wootton, Mavuto Mukaka, Jacqui Montgomery, Noel Kayange, Phillips Chimpeni, Dyfrig A Hughes, Malcolm E Molyneux, Steve A Ward, Peter A Winstanley, David G Lalloo. Measurement of adherence, drug concentrations and the effectiveness of artemether-lumefantrine, chlorproguanil-dapsone or sulphadoxine-pyrimethamine in the treatment of uncomplicated malaria in Malawi. Malaria journal. 2009 Aug; 8(?):204. doi: 10.1186/1475-2875-8-204. [PMID: 19709418]
  • Fabrice Nesslany, Sophie Simar-Meintières, Hervé Ficheux, Daniel Marzin. Aloe-emodin-induced DNA fragmentation in the mouse in vivo comet assay. Mutation research. 2009 Aug; 678(1):13-9. doi: 10.1016/j.mrgentox.2009.06.004. [PMID: 19559101]
  • Itsuko Fukuda, Atsushi Kaneko, Shin Nishiumi, Masaya Kawase, Rika Nishikiori, Nobuhide Fujitake, Hitoshi Ashida. Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Journal of bioscience and bioengineering. 2009 Mar; 107(3):296-300. doi: 10.1016/j.jbiosc.2008.10.008. [PMID: 19269596]
  • Chakradhara Rao Uppugunduri Satyanarayana, Anichavezhi Devendran, Muthukumaran Jayaraman, Jayakanthan Mannu, Premendu P Mathur, Shewade Deepak Gopal, Krishnamoorthy Rajagopal, Adithan Chandrasekaran. Influence of the genetic polymorphisms in the 5' flanking and exonic regions of CYP2C19 on proguanil oxidation. Drug metabolism and pharmacokinetics. 2009; 24(6):537-48. doi: 10.2133/dmpk.24.537. [PMID: 20045989]
  • Christine Payen, Luc Monnin, Corine Pulce, Jacques Descotes. Bone marrow aplasia following acute poisoning with chloroquine-proguanil. Clinical toxicology (Philadelphia, Pa.). 2008 Dec; 46(10):1085-7. doi: 10.1080/15563650601182925. [PMID: 19065311]
  • Evandro L Duarte, Tiago R Oliveira, Daiane S Alves, Vicente Micol, M Teresa Lamy. On the interaction of the anthraquinone barbaloin with negatively charged DMPG bilayers. Langmuir : the ACS journal of surfaces and colloids. 2008 Apr; 24(8):4041-9. doi: 10.1021/la703896w. [PMID: 18318556]
  • . Artemether + lumefantrine: new drug. An alternative to atovaquone + proguanil. Prescrire international. 2008 Apr; 17(94):54-6. doi: . [PMID: 18516806]
  • N Thorogood, S Atwal, W Mills, M Jenner, D A Lewis, J D Cavenagh, S G Agrawal. The risk of antimalarials in patients with renal failure. Postgraduate medical journal. 2007 Dec; 83(986):e8. doi: 10.1136/pgmj.2007.063735. [PMID: 18057166]
  • Pilar Foronda, María A Santana-Morales, Jorge Orós, Néstor Abreu-Acosta, Antonio Ortega-Rivas, Jacob Lorenzo-Morales, Basilio Valladares. Clinical efficacy of antiparasite treatments against intestinal helminths and haematic protozoa in Gallotia caesaris (lizards). Experimental parasitology. 2007 Aug; 116(4):361-5. doi: 10.1016/j.exppara.2007.02.004. [PMID: 17399704]
  • Wen-Fu Tang, Qin Yu, Mei-Hua Wan, Feng Qin, Yong-Gang Wang, Guang-Yuan Chen, Mao-Zhi Liang, Xi Huang. Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography. Biomedical chromatography : BMC. 2007 Jul; 21(7):701-7. doi: 10.1002/bmc.808. [PMID: 17370297]
  • Rosa E Moo-Puc, Gonzalo J Mena-Rejon, Leovigildo Quijano, Roberto Cedillo-Rivera. Antiprotozoal activity of Senna racemosa. Journal of ethnopharmacology. 2007 Jun; 112(2):415-6. doi: 10.1016/j.jep.2007.03.028. [PMID: 17481835]
  • Dongming Yan, Yueming Ma. Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection. Biomedical chromatography : BMC. 2007 May; 21(5):502-7. doi: 10.1002/bmc.784. [PMID: 17294506]
  • Leena Laitinen, Elina Takala, Heikki Vuorela, Pia Vuorela, Ann Marie Kaukonen, Martti Marvola. Anthranoid laxatives influence the absorption of poorly permeable drugs in human intestinal cell culture model (Caco-2). European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2007 Apr; 66(1):135-45. doi: 10.1016/j.ejpb.2006.09.006. [PMID: 17098405]
  • Tewari Tushar, Thomas Vinod, Sundaram Rajan, Chanolean Shashindran, Chandrasekaran Adithan. Effect of honey on CYP3A4, CYP2D6 and CYP2C19 enzyme activity in healthy human volunteers. Basic & clinical pharmacology & toxicology. 2007 Apr; 100(4):269-72. doi: 10.1111/j.1742-7843.2006.00039.x. [PMID: 17371531]
  • Lise Musset, Olivier Bouchaud, Sophie Matheron, Laurent Massias, Jacques Le Bras. Clinical atovaquone-proguanil resistance of Plasmodium falciparum associated with cytochrome b codon 268 mutations. Microbes and infection. 2006 Sep; 8(11):2599-604. doi: 10.1016/j.micinf.2006.07.011. [PMID: 16962361]
  • R McGready, K Stepniewska, S A Ward, T Cho, G Gilveray, S Looareesuwan, N J White, F Nosten. Pharmacokinetics of dihydroartemisinin following oral artesunate treatment of pregnant women with acute uncomplicated falciparum malaria. European journal of clinical pharmacology. 2006 May; 62(5):367-71. doi: 10.1007/s00228-006-0118-y. [PMID: 16552504]
  • Nathalie L Leveque, William N Charman, Francis C K Chiu. Sensitive method for the quantitative determination of proguanil and its metabolites in rat blood and plasma by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jan; 830(2):314-21. doi: 10.1016/j.jchromb.2005.11.004. [PMID: 16310420]
  • Katarzyna Skupińska, Monika Zylm, Irena Misiewicz, Teresa Kasprzycka-Guttman. Interaction of anthracene and its oxidative derivatives with human serum albumin. Acta biochimica Polonica. 2006; 53(1):101-12. doi: . [PMID: 16404478]
  • Jørgen A L Kurtzhals. [Ineffective change of antimalaria prophylaxis to Artemisia vulgaris in a group travelling to West Africa]. Ugeskrift for laeger. 2005 Oct; 167(43):4082-3. doi: ". [PMID: 16251093]
  • M D Edstein, B M Kotecka, K L Anderson, D J Pombo, D E Kyle, K H Rieckmann, M F Good. Lengthy antimalarial activity of atovaquone in human plasma following atovaquone-proguanil administration. Antimicrobial agents and chemotherapy. 2005 Oct; 49(10):4421-2. doi: 10.1128/aac.49.10.4421-4422.2005. [PMID: 16189139]
  • K Na-Bangchang, C Manyando, R Ruengweerayut, D Kioy, M Mulenga, G B Miller, J Konsil. The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women. European journal of clinical pharmacology. 2005 Sep; 61(8):573-82. doi: 10.1007/s00228-005-0969-7. [PMID: 16041597]
  • John Teilmann Larsen, Kim Brøsen. Consumption of charcoal-broiled meat as an experimental tool for discerning CYP1A2-mediated drug metabolism in vivo. Basic & clinical pharmacology & toxicology. 2005 Sep; 97(3):141-8. doi: 10.1111/j.1742-7843.2005.pto_97365.x. [PMID: 16128907]
  • N Lindegårdh, D Blessborn, Y Bergqvist. Simultaneous quantitation of the highly lipophilic atovaquone and hydrophilic strong basic proguanil and its metabolites using a new mixed-mode SPE approach and steep-gradient LC. Journal of chromatographic science. 2005 May; 43(5):259-66. doi: 10.1093/chromsci/43.5.259. [PMID: 15975245]
  • Bo-Kyung Sung, Moo-Key Kim, Wang-Hyu Lee, Dong-Heon Lee, Hoi-Seon Lee. Growth responses of Cassia obtusifolia toward human intestinal bacteria. Fitoterapia. 2004 Jul; 75(5):505-9. doi: 10.1016/j.fitote.2004.03.012. [PMID: 15261390]
  • Yong-Soo Kwon, Jae-Young Koh, Dong-Keun Song, Hyoung-Chun Kim, Myung-Sang Kwon, Yeon-Sik Choi, Myung-Bok Wie. Danthron inhibits the neurotoxicity induced by various compounds causing oxidative damages including beta-amyloid (25-35) in primary cortical cultures. Biological & pharmaceutical bulletin. 2004 May; 27(5):723-6. doi: 10.1248/bpb.27.723. [PMID: 15133254]
  • L D Kong, Christopher H K Cheng, R X Tan. Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. Journal of ethnopharmacology. 2004 Apr; 91(2-3):351-5. doi: 10.1016/j.jep.2004.01.013. [PMID: 15120460]
  • Jochen Wiesner, Regina Ortmann, Hassan Jomaa, Martin Schlitzer. New antimalarial drugs. Angewandte Chemie (International ed. in English). 2003 Nov; 42(43):5274-93. doi: 10.1002/anie.200200569. [PMID: 14613157]
  • Janelle M Hoskins, Gillian M Shenfield, Annette S Gross. Concordance between proguanil phenotype and CYP2C19 genotype in Chinese. European journal of clinical pharmacology. 2003 Nov; 59(8-9):611-4. doi: 10.1007/s00228-003-0665-4. [PMID: 13680037]
  • R McGready, K Stepniewska, E Seaton, T Cho, D Cho, A Ginsberg, M D Edstein, E Ashley, S Looareesuwan, N J White, F Nosten. Pregnancy and use of oral contraceptives reduces the biotransformation of proguanil to cycloguanil. European journal of clinical pharmacology. 2003 Oct; 59(7):553-7. doi: 10.1007/s00228-003-0651-x. [PMID: 12955370]
  • R McGready, K Stepniewska, M D Edstein, T Cho, G Gilveray, S Looareesuwan, N J White, F Nosten. The pharmacokinetics of atovaquone and proguanil in pregnant women with acute falciparum malaria. European journal of clinical pharmacology. 2003 Oct; 59(7):545-52. doi: 10.1007/s00228-003-0652-9. [PMID: 12955371]
  • Eskild Petersen. The safety of atovaquone/proguanil in long-term malaria prophylaxis of nonimmune adults. Journal of travel medicine. 2003 May; 10 Suppl 1(?):S13-5; discussion S21. doi: 10.2310/7060.2003.35050. [PMID: 12737755]
  • Kristian Kofoed, Eskild Petersen. The efficacy of chemoprophylaxis against malaria with chloroquine plus proguanil, mefloquine, and atovaquone plus proguanil in travelers from Denmark. Journal of travel medicine. 2003 May; 10(3):150-4. doi: 10.2310/7060.2003.35746. [PMID: 12757688]
  • E A Anteyi, H M Liman, A Gbaji. Malaria prophylaxis in post renal transplant recipients in the tropics: is it necessary?. The Central African journal of medicine. 2003 May; 49(5-6):63-6. doi: . [PMID: 15214285]
  • Timothy M E Davis, David A Syed, Kenneth F Ilett, P Hugh R Barrett. Toxicity related to chloroquine treatment of resistant vivax malaria. The Annals of pharmacotherapy. 2003 Apr; 37(4):526-9. doi: 10.1345/aph.1c311. [PMID: 12659609]
  • Geoff A Butcher, Robert E Sinden. Persistence of atovaquone in human sera following treatment: inhibition of Plasmodium falciparum development in vivo and in vitro. The American journal of tropical medicine and hygiene. 2003 Jan; 68(1):111-4. doi: 10.4269/ajtmh.2003.68.111. [PMID: 12556158]
  • C P Babalola, G B Iwheye, A A Olaniyi. Effect of proguanil interaction on bioavailability of cloxacillin. Journal of clinical pharmacy and therapeutics. 2002 Dec; 27(6):461-4. doi: 10.1046/j.1365-2710.2002.00446.x. [PMID: 12472986]
  • S Gupta, T Chaudhuri, P Seth, D K Ganguly, A K Giri. Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays. Phytotherapy research : PTR. 2002 Nov; 16(7):655-61. doi: 10.1002/ptr.1038. [PMID: 12410547]
  • F Bruneel, B Gachot, M Wolff, J P Bedos, B Regnier, M Danis, F Vachon. [Blackwater fever]. Presse medicale (Paris, France : 1983). 2002 Sep; 31(28):1329-34. doi: NULL. [PMID: 12355996]
  • Ausra Nemeikaite-Ceniene, Egle Sergediene, Henrikas Nivinskas, Narimantas Cenas. Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2002 Sep; 57(9-10):822-7. doi: 10.1515/znc-2002-9-1012. [PMID: 12440719]
  • Mita M Thapar, Michael Ashton, Niklas Lindegårdh, Yngve Bergqvist, Sabina Nivelius, Inger Johansson, Anders Björkman. Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis. European journal of clinical pharmacology. 2002 Apr; 58(1):19-27. doi: 10.1007/s00228-002-0426-9. [PMID: 11956669]
  • Jean François Chaulet, Patrice Nony, Fabien Bévalot, Pascal Girard, Sylvie Chabaud, Cyril Mounier, Pascal Clair, Jean Pierre Boissel, Gilles Grelaud. Bioequivalence evaluation of a fixed combination of chloroquine and proguanil in a capsule formulation versus a standard medication. Arzneimittel-Forschung. 2002; 52(5):407-12. doi: 10.1055/s-0031-1299906. [PMID: 12087928]
  • H Matsuda, H Shimoda, T Morikawa, M Yoshikawa. Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorganic & medicinal chemistry letters. 2001 Jul; 11(14):1839-42. doi: 10.1016/s0960-894x(01)00318-3. [PMID: 11459643]
  • R B Taylor, R G Reid, A S Low. Analysis of proguanil and its metabolites by application of the sweeping technique in micellar electrokinetic chromatography. Journal of chromatography. A. 2001 May; 916(1-2):201-6. doi: 10.1016/s0021-9673(00)01035-9. [PMID: 11382292]
  • S J Semple, S M Pyke, G D Reynolds, R L Flower. In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus. Antiviral research. 2001 Mar; 49(3):169-78. doi: 10.1016/s0166-3542(01)00125-5. [PMID: 11428243]
  • B Høgh, P D Clarke, D Camus, H D Nothdurft, D Overbosch, M Günther, I Joubert, K C Kain, D Shaw, N S Roskell, J D Chulay. Atovaquone-proguanil versus chloroquine-proguanil for malaria prophylaxis in non-immune travellers: a randomised, double-blind study. Malarone International Study Team. Lancet (London, England). 2000 Dec; 356(9245):1888-94. doi: 10.1016/s0140-6736(00)03260-8. [PMID: 11130385]
  • K Herrlin, A Y Massele, G Rimoy, C Alm, M Rais, O Ericsson, L Bertilsson, L L Gustafsson. Slow chloroguanide metabolism in Tanzanians compared with white subjects and Asian subjects confirms a decreased CYP2C19 activity in relation to genotype. Clinical pharmacology and therapeutics. 2000 Aug; 68(2):189-98. doi: 10.1067/mcp.2000.108583. [PMID: 10976550]
  • G A Butcher, J Mendoza, R E Sinden. Inhibition of the mosquito transmission of Plasmodium berghei by Malarone (atovaquone-proguanil). Annals of tropical medicine and parasitology. 2000 Jul; 94(5):429-36. doi: 10.1080/00034983.2000.11813561. [PMID: 10983555]
  • E Petersen, T Ronne, A Ronn, I Bygbjerg, S O Larsen. Reported side effects to chloroquine, chloroquine plus proguanil, and mefloquine as chemoprophylaxis against malaria in Danish travelers. Journal of travel medicine. 2000 Mar; 7(2):79-84. doi: 10.2310/7060.2000.00026. [PMID: 10759574]
  • S Enosse, G A Butcher, G Margos, J Mendoza, R E Sinden, B Høgh. The mosquito transmission of malaria: the effects of atovaquone-proguanil (Malarone) and chloroquine. Transactions of the Royal Society of Tropical Medicine and Hygiene. 2000 Jan; 94(1):77-82. doi: 10.1016/s0035-9203(00)90447-4. [PMID: 10748906]
  • L Tennezé, C Verstuyft, L Becquemont, J M Poirier, G R Wilkinson, C Funck-Brentano. Assessment of CYP2D6 and CYP2C19 activity in vivo in humans: a cocktail study with dextromethorphan and chloroguanide alone and in combination. Clinical pharmacology and therapeutics. 1999 Dec; 66(6):582-8. doi: 10.1053/cp.1999.v66.103401001. [PMID: 10613613]
  • K Kågedal, D Bironaite, K Ollinger. Anthraquinone cytotoxicity and apoptosis in primary cultures of rat hepatocytes. Free radical research. 1999 Nov; 31(5):419-28. doi: 10.1080/10715769900300981. [PMID: 10547186]
  • J A Kolawole, A Mustapha, I Abdul-Aguye, N Ochekpe, R B Taylor. Effects of cimetidine on the pharmacokinetics of proguanil in healthy subjects and in peptic ulcer patients. Journal of pharmaceutical and biomedical analysis. 1999 Sep; 20(5):737-43. doi: 10.1016/s0731-7085(99)00058-8. [PMID: 10701981]
  • M van Vugt, M D Edstein, S Proux, K Lay, M Ooh, S Looareesuwan, N J White, F Nosten. Absence of an interaction between artesunate and atovaquone--proguanil. European journal of clinical pharmacology. 1999 Aug; 55(6):469-74. doi: 10.1007/s002280050658. [PMID: 10492061]
  • C Gillotin, J P Mamet, L Veronese. Lack of a pharmacokinetic interaction between atovaquone and proguanil. European journal of clinical pharmacology. 1999 Jun; 55(4):311-5. doi: 10.1007/s002280050634. [PMID: 10424325]
  • G Anabwani, C J Canfield, D B Hutchinson. Combination atovaquone and proguanil hydrochloride vs. halofantrine for treatment of acute Plasmodium falciparum malaria in children. The Pediatric infectious disease journal. 1999 May; 18(5):456-61. doi: 10.1097/00006454-199905000-00011. [PMID: 10353520]
  • S O Mueller, M Schmitt, W Dekant, H Stopper, J Schlatter, P Schreier, W K Lutz. Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1999 May; 37(5):481-91. doi: 10.1016/s0278-6915(99)00027-7. [PMID: 10456676]
  • M Beerahee. Clinical pharmacology of atovaquone and proguanil hydrochloride. Journal of travel medicine. 1999 May; 6 Suppl 1(?):S13-7. doi: . [PMID: 23573547]